Dallacker [1] reports the synthesis of dimethoxy-methylenedioxy-allylbenzenes including pseudo-dillapiole (Dallacker's pseudo-dillapiole compound 8f, 4,5-dimethoxy-2,3-methylenedioxy-1-allyl-benzene) and nor pseudo-dillapiole (Dallacker's compound 8e, 6-methoxy-2,3-methylenedioxy-4-allyl-phenol) two of the dimethoxy compounds encompassed in Applicants' genus. Dallacker also shows a number of position isomers of some of Applicants' compounds, including dillapiole (Dallacker's "Dill Apiole", 2,3-Dimethoxy-4,5-methylenedioxy-allyl-benzene), apiole (Dallacker's compound 7, 5,6-dimethoxy-2,3-methylenedioxy-allyl-benzene), 2,5-dimethoxy-3,4-methylenedioxy-allyl-benzene (Dallacker's "Petersilen-Apiol"), 4,6-dimethoxy-2,3-methylenedioxy-allyl-benzene (Dallacker's compound 4i), and 2,6-dimethoxy-3,4-methylenedioxy-allyl-benzene (Dallacker's compound 5i). Dallacker also shows monomethoxy, allyloxy, hydroxy (allyl-phenol), nitro, amino, acetamino, and propenyl derivatives.
However, Dallacker neither shows nor suggests any biological activity, much less antimicrobial or antifungal properties.
Several methylenedioxyphenyl compounds and the compound dillapiole 5,6-dimethoxy-3,4-methylenedioxy-1-allyl benzene, were reported by Devakumar, et al. [2], and in an Indian patent [3], No. 128,129 (1969) to have synergic activity with pyrethrum insecticides.
In the provisional specification of the Indian patent No. 128,129 attention was focused on the propyl analog of dillapiole because of undesirable physiologic side effects of the allyl side chain. The allyl side chain was hydrogenated in the presence of a Raney-nickel catalyst, and the resulting di-hydrogenated compound was found to be an effective synergic with pyrethrins against houseflies, cockroaches and flour beetles.
Citrus Canker is a deadly plant disease caused by Xanthomonas campestris pv. citrii. This disease causes millions of dollars damage to citrus crops in the work each year, adversely affecting the world food supply. Currently, the only solution is containment by isolation/removal of the diseased plants, followed by burning the groves. A recent newspaper article (S. F. Chronicle Feb. 18, 1986, p. 17) reports that a serum of "old beer and bacteria" developed by RAM Chemical of Borger TX is claimed to be 100% effective in stopping outbreaks of canker.
Wheat powdery mildew (WPM) is a fungal pathovar, Erysiphe graminis, that causes extensive damage to wheat crops. A variety of compounds are used to combat these diseases. For example, wheat is treated with duPont's BENOMYL, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbonate, Farbenfabriken Bayer's EDIFENPHOS, O-ethyl-S,S-diphenyl-dithiophosphate, and Bayer AG/Mobay Chemical Company's BAYLETON, 1-(4-chlorophenoxy)-3,3-dimethoxy-1-(1H-1,2,4-triazol-1-yl)-2-butanone. However, the Edifenphos cannot be sold or used in the U.S., is toxic to fish, should not be mixed with alkaline materials, and cannot be used within 10 days before or after a propanil application. Benomyl is likewise toxic to fish, livestock may not be grazed on treated areas, it should not become wet during storage or combined with alkaline pesticides and apples do not express fine fruit finish. Bayleton exhibits some plant stunting and deformation on ornamentals when used at excessive rates and is toxic to fish.
There is thus a need for new compounds which are effective against such plant diseases.